Transition Metal Catalyzed Cycloadditions: An Intramolecular [4 + 4] Cycloaddition Strategy for the Efficient Synthesis of Dicyclopenta[a,d]cyclooctene 5-8-5 Ring Systems

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 4908-4909

  Wender, Paul A ^a   Nuss, John M ^a   Smith, David B ^a   Suárez Sobrino, Angel ^a   Vågberg, Jan ^a   Decosta, Debra ^b   Bordner, Jon ^b  

^a STANFORD UNIVERSITY   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; FUSICOCCIN; SESTERTERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; MASS SPECTROMETRY; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030790366     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970841x     Document Type: Article

References (56)

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24. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
25. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
26. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
27. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
28. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
29. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
30. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
31. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
32. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
33. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
34. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
35. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
36. For recent syntheses of eight-membered carbocycles and leading references, see: (a) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. (c) Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730. (d) Miller S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. (e) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720. (f) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J. Am. Chem. Soc. 1996, 118, 10803. (g) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980. (h) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (i) Lange, G. L.; Organ, M. G. J. Am. Chem. Soc. 1996, 61, 5358. (j) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478. (k) Chase, C. E.; Bender, J. A.; West, F. G. Synlett 1996, 1173 and refs 5-9 above. For reviews, see: (l) Petasis, N. A.; Patane, M.A. Tetrahedron 1992, 48, 5757. (m) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251. (n) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
37. (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678.
38. (b) Wender, P. A.; Snapper, M. L. Tetrahedron Lett. 1987, 28, 2221.
39. (c) Wender, P. A.; Ihle, N. C. Tetrahedron Lett. 1987, 28, 2451.
40. (d) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904.
41. (e) Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089.
42. J. Nuss, Stanford University, unpublished results. The procedure follows that given in: Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523.
43. J. Nuss, Stanford University, unpublished results. The procedure follows that given in: Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523.
44. (a) Julia, M.; Julia, S.; Stalla-Bourdillon, B.; Descoins, C. Bull. Soc. Chim. Fr. 1964, 2533.
45. (b) Taber, D. F.; Campbell, C.; Gunn, B. P.; Chiu, I.-C. Tetrahedron Lett. 1981, 51, 5141.
46. (c) Shishido, K.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1986, 27, 1167.
47. Satisfactory NMR spectra and combustion analyses or high-resolution mass spectra were obtained for all new compounds.
48. Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
49. The use of different proportions of EE and ZE isomers of bisdiene 4 led to similar results.
50. Brown, H. C.; Knights, E. F.; Scouten, C. G. J. Am. Chem. Soc. 1974, 96, 7765.
51. (a) Negishi, E.; Matsushita, S.; Chatterjee, S.; John, R. A. J. Org. Chem. 1982, 47, 3188.
52. (b) Wender, P. A.; Fisher, K. Tetrahedron Lett. 1986, 27, 1857.
53. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett. 1976, 2975.
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55. For a representative alternative synthetic strategy that addresses the side-chain stereochemistry problem, see: Guevel, A.-C.; Hart, D. J. J. Org. Chem. 1996, 61, 465.
56. The author has deposited atomic coordinates for 10 with the Cambridge Crystallographic Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.